You don’t get to take unlimited big bets in a single lifetime. You get a small number of windows where risk tolerance, energy, capital, and conviction align.
In The Black Swan Nassim Taleb frames this as asymmetric exposure to unlimited upside with limited downside. And startups are one of the clearest modern mechanisms for that kind of asymmetry. But what’s often missed is that these opportunities are finite. You can’t swing endlessly. Most of life is spent accumulating the resources—knowledge, capital, relationships—that make the next swing possible.
What follows are six moments where those resources briefly line up.
I thought I was cool
Walking to Equinox Soho
In my Canada Goose
At 0 degrees in the Manhattan Winter
Only for my panache to crumple instantly
As a pleasant cigarette smoke wafted into my nose
From a nameless dark man
In a thrifted French beret
And cheap leather jacket
Eclipsing me like I was nothing
As he read Poe out of a hardback
Draped on the ground
Over the nondescript metal stairs
Between John Fluevog and Prince Street Pizza
Effortless
Maybe here he had found the meaning of life
And the Equinox was fucking closed
I’ve been chatting with a few female friends about dating.
Dating in New York, they say, feels like every guy operates with the emotional depth of a vending machine: Insert coin, select option A (situationship) or B (serious), dispense relationship if available.
Meanwhile, I’ve had conversations with guys who brag about “only doing long-term relationships” as if it’s a personality trait, a mark of maturity, and “situationships” are beneath them. There’s some cognitive dissonance between these two observations, and it got me thinking about how I understood relationships when I was younger, and how I suspect many men still do.
I think for a lot of men their understanding of relationships stops developing shortly after high school.
Reverberations:
Waves flooding a hollow trunk
floating in a rice field. 1
The husk splits,
roots finally spreading
into soil I’ve been taught to reject,
for it was, after all, beneath me.
How hard it is
to support yourself
with both feet off the ground.
I am bamboo now-
hungry for growth,
nourished by the music
of both earths
that claimed I didn’t belong.
Eyes open
to the melody I’d always been:
not broken, not foreign—
the indigenous harmony
of in-between.
Author’s note: This poem alludes to the shame I felt of being an outsider, Chinese, growing up in a predominantly white community, and my recent coming to terms with and becoming proud of being Chinese.
A reference to Jay Chou’s 稻香 that I had been listening to ↩︎
